On Tue, Dec 08, 2015 at 04:03:59PM +0100, W. Martin Borgert wrote:
> >There is also a hint for iceowl-extension on not remebered passwords,
> >maybe this is issue?
> >
> >https://wiki.debian.org/Icedove#Iceowl-extension_does_not_remember_credentials
> 
> This is problably the cause of the message, that I related
> wrongly to the SMTP sending failure.
> 
> I wonder what your SMTP config is? Mine is:
> 
> Server: mydomain.com
> Port: 587
> Username: username
> Auth method: NTLM
> Security: STARTTLS

We use slightly the same configuration except small differences, but we got
also a load balancer between me and the exchange backend.

Security:       STARTTLS
Authentication: password, normal
Port:           25 (instead of 587)

But I assume that the NTLM authentication is the origin of your
trouble. If possible try out SSL/TLS instead of NTLM. I can remember
that at least for old samaba servers (that can't handle NTLM v2) I had
to allow NTLM v1 on the local lan. But that's something you really don't
want to do in company areas.

This old article I found on the microsoft site.
https://support.microsoft.com/en-us/kb/976918

Regards
Carsten

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